Acid-base strength in N,N-dimethylformamide

Kolthoff, I. M.; Chantooni, M. K.; Smagowski, Henryk

doi:10.1021/ac60295a013

Cited by 84 publications

(58 citation statements)

References 19 publications

(4 reference statements)

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“…For example, the dielectric constant of (aprotic) 1-methylimidazole indicates it is a polar liquid, even if its value is frequency dependent (e.g., e = 21.5 at 5.8 GHz and 32.3 at 2.45 GHz). [123] Addition of HX (X = Cl À , Br À ) does not lead to sol- 14.5 [73] 25.9 [73] 1.99 [71] --17.2 [73] -CH 3 OH 1606.4 [c] 29.0 [1] À2.4 [74] 15.5 [1] -% 16.5 [30] --CH 3 [15] 12.3 [1] 23.51 [2] 4.75 [33] 10.3 [78] 9.52 [79] 13.5 [80] ClCH 2 CO 2 H 1408 [18] 9.00 [81] 18.8 [82] 2.81 [82] 8.3 [82] 7.8 [82] 10.1 [82] -C 6 H 5 CO 2 H 1400 [c] 11.0 [83] 20.7 [83] 4.2 [83] 10.25 [84] 9.4 [85] 12.3 [83] 4.20 [86] HCl 1396 [15] 1.8 [1] 8.9 [2] À8 [33] 2.08 [87] 1.23 [88] 3.55 [89] - -6.67 [91] 5.88 [91] 9.03 [91] -H 3 PO 4 1383 [33] --2.10…”

Section: Protic Molecules In Molecular Liquidsmentioning

confidence: 99%

“…2.5 [93] 10.75 [2] 0.65 [94] 5.46 [98] 4.9 [96] --CF 3 CO 2 H 1352.1 [c] 3.51 [99] 12.65 [2] 0.00 [90] ----H 2 SO 4 1295 [20] 1.99 [100] 7.29 [101] À9 [33] -1.62 [102] 3.1 [80] HOTf 1278 [33] 0.3 [1] /f.d.…”

Section: Protic Molecules In Molecular Liquidsmentioning

confidence: 99%

“…13.2 [107] 23.3 [108] 13.6 [108] -13.2 [108] 13.65 [80] 15.3 [106] [(C 2 H 5 ) 3 NH] + 981.8 [109] 9.0 [73] 18.82 [104] 10.7 [110] -10.9 [108] 9.25 [80] 12.5 [106] [Hmim]…”

Section: Protic Molecules In Molecular Liquidsmentioning

confidence: 99%

“…---0.01 [90] --29.4 [118] -[NH 4 ] + 854 [15] 10.5 [1] 16.46 [114] 9.24 [33] -10.8 [115] 9.45 [80] -…”

Section: Protic Molecules In Molecular Liquidsmentioning

confidence: 99%

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Brønsted Acidity and the Medium: Fundamentals with a Focus on Ionic Liquids

2011

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Fundamental aspects of Brønsted acidity in ionic liquid systems, in relation to those of simple protic molecules in the gas phase, pure protic molecules in the condensed phase and solutions of protic molecules in molecular systems, are presented. The variety of acidities possible, beyond those observed in aqueous systems, is emphasised and discussed in terms of differences of solvent levelling, ionisation, dissociation, homo-/hetero-conjugate ion speciation and the stabilisation of proton-transfer products from solvent to solvent. It is argued that data regarding aqueous systems do not necessarily explain acid/base behaviour in other liquids satisfactorily. Methods of measuring acidity are reviewed, particularly by spectrophotometry and electrochemistry and recommendations proffered for estimating speciation and acidity of ionic liquids of various complexities.

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Section: Protic Molecules In Molecular Liquidsmentioning

confidence: 99%

Section: Protic Molecules In Molecular Liquidsmentioning

confidence: 99%

“…13.2 [107] 23.3 [108] 13.6 [108] -13.2 [108] 13.65 [80] 15.3 [106] [(C 2 H 5 ) 3 NH] + 981.8 [109] 9.0 [73] 18.82 [104] 10.7 [110] -10.9 [108] 9.25 [80] 12.5 [106] [Hmim]…”

Section: Protic Molecules In Molecular Liquidsmentioning

confidence: 99%

“…---0.01 [90] --29.4 [118] -[NH 4 ] + 854 [15] 10.5 [1] 16.46 [114] 9.24 [33] -10.8 [115] 9.45 [80] -…”

Section: Protic Molecules In Molecular Liquidsmentioning

confidence: 99%

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Brønsted Acidity and the Medium: Fundamentals with a Focus on Ionic Liquids

2011

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“…The exact concentration of the DTG solution was determined by titration with standardized 0.1N HC1; before use, DMF was distilled from NaOH as described. 24 The number of titratable groups in a coagulated membrane was measured by back-titration of the amount of acid displaced from a membrane previously converted into its acid salt. A 47 mm diameter membrane disk was soaked extensively in 1.ONHC1 and washed well with ethanol to remove unbound acid.…”

Section: Acid-base Titration Of Polymeric Aryl Amines and Pyridinesmentioning

confidence: 99%

Acrylonitrile-based copolymers: Synthesis, characterization, and formation of ultrafiltration membranes utilized for the immobilization of proteins

Dalven¹,

Hildebrandt²,

Shamir³

et al. 1985

J. Appl. Polym. Sci.

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SynopsisVarious high molecular weight copolymers of acrylonitrile and a vinyl comonomer containing an aryl amine, a pyridine, or a n aliphatic hydroxyl group were synthesized via slurry polymerization techniques so as to contain from 1 to 15 mol % functional comonomer. The comonomer content was quantitated by ultraviolet absorbance, base titration of acid polymer salts, and/or relative chemical reactivity with trichloro-s-triazine. Thin films were cast from copolymer solutions, coagulated into unsupported ultrafiltration membranes, and characterized with respect to both water permeability and pore size distribution. Analysis by size exclusion chromatography of the membrane permeate of a pool of dextran fractions yielded a continuous distribution curve for membrane pore size over the range 1.5 to 70 nm. The ultrafiltration membranes were used for protein immobilization after appropriate chemical activation. The three distinct types of functional copolymers gave comparable results for achymotrypsin, with protein weight loadings of 6-12% and 4045% retention of enzymatic specific activity.

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Acid Base Reactions Between Acridine Orange and Substituted Phenols in Benzonitrile Part I. Thermodynamics of Association and Ionic Equilibria

Süttinger

Strohbusch

1984

Ber Bunsenges Phys Chem

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Proton transfer reactions of the five substituted phenols 3‐Cl−4‐nitrophenol CNP, 4‐nitrophenol NP, 3‐methyl−4‐nitrophenol MNP, 4‐Cl−3,5‐dimethylphenol CMP, and 3,5‐dimethylphenol DMP with acridine orange, and the formation of hydrogen bonded complexes AHA− of the anions A− of CNP, NP, and MNP with the respective phenols AH in benzonitrile solution were investigated by means of absorption spectroscopy. Thermodynamic data for the formation of the complexes AHA− and of the ionic reactions (1) and (2) of CNP, NP, and MNP with the acridine orange base B and for the reactions (2) and (3) of CMP and DMP with B were determined. The reactions (1) ‐ (3) are exothermic. The absolute values of ΔH1 increase with the acidity of the phenols. The formation enthalpies of the hydrogen bonded anions AHA‐ are much larger than ΔH1, so that ΔH2 is mainly determined by this association. On the other hand there is no significant difference between ΔH2 and ΔH3; thus the hydrogen bond formed between a phenol and a complexed anion AHA‐ is very weak. Substituent effects on the acidity of phenols are about twice as large in benzonitrile as in aqueous solution.

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Acid-base strength in N,N-dimethylformamide

Cited by 84 publications

References 19 publications

Brønsted Acidity and the Medium: Fundamentals with a Focus on Ionic Liquids

Brønsted Acidity and the Medium: Fundamentals with a Focus on Ionic Liquids

Acrylonitrile-based copolymers: Synthesis, characterization, and formation of ultrafiltration membranes utilized for the immobilization of proteins

Acid Base Reactions Between Acridine Orange and Substituted Phenols in Benzonitrile Part I. Thermodynamics of Association and Ionic Equilibria

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